WO2015198985A1 - Gel humide et son procédé de fabrication - Google Patents

Gel humide et son procédé de fabrication Download PDF

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Publication number
WO2015198985A1
WO2015198985A1 PCT/JP2015/067728 JP2015067728W WO2015198985A1 WO 2015198985 A1 WO2015198985 A1 WO 2015198985A1 JP 2015067728 W JP2015067728 W JP 2015067728W WO 2015198985 A1 WO2015198985 A1 WO 2015198985A1
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wet gel
liquid
silicone resin
parts
wet
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PCT/JP2015/067728
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English (en)
Japanese (ja)
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千尋 浦田
篤 穂積
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国立研究開発法人産業技術総合研究所
千尋 浦田
篤 穂積
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Application filed by 国立研究開発法人産業技術総合研究所, 千尋 浦田, 篤 穂積 filed Critical 国立研究開発法人産業技術総合研究所
Priority to KR1020167036177A priority Critical patent/KR101974984B1/ko
Priority to US15/319,924 priority patent/US10023701B2/en
Priority to EP15811115.3A priority patent/EP3162857B1/fr
Priority to JP2016529542A priority patent/JP6245714B2/ja
Priority to CN201580033541.7A priority patent/CN106574119B/zh
Publication of WO2015198985A1 publication Critical patent/WO2015198985A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C08J3/092—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C08J3/075—Macromolecular gels
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
    • C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
    • C08J3/098—Other compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K11/00—Use of ingredients of unknown constitution, e.g. undefined reaction products
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/01—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
    • C08J2383/04—Polysiloxanes

Definitions

  • the present invention relates to a wet gel, a method for producing a wet gel, and an article.
  • Patent Document 1 discloses an article having a slippery surface.
  • the article has at least one surface comprising a supramolecular polymer and a lubricating liquid.
  • the supramolecular polymer and the lubricating liquid have an affinity for each other such that they are absorbed into the supramolecular polymer in an amount sufficient to form a slippery lubricating layer on the surface of the supramolecular polymer swollen by the lubricating liquid.
  • Patent Document 1 since a slippery lubricating layer is formed on the surface of the supramolecular polymer swollen by the lubricating liquid, the lubricating liquid is limited to a liquid having a predetermined affinity for the supramolecular polymer. Moreover, in patent document 1, the adhesive force with respect to ice is 4 kPa, and difficult adhesion is inadequate. Further, in Patent Document 1, since the lubricating layer cannot be spontaneously formed, the lubricating layer is not regenerated when the lubricating layer is wiped off.
  • the liquid to be introduced is not limited to a liquid having a predetermined affinity for the polymer, and is excellent in difficult adhesion and can be separated spontaneously. It is an object to provide a wet gel.
  • spontaneous separation is not limited to separation due to internal factors (for example, decreased affinity, liquid volatilization), but is caused by external stimulation (for example, temperature, chemical reaction). Including.
  • One embodiment of the present invention includes a crosslinked silicone resin in which a silicone resin composition is cured in a wet gel, a first liquid capable of dissolving the silicone resin composition, and a solution in the first liquid. Or a second liquid having a degree of swelling when the crosslinked silicone resin is immersed in n-dodecane that is less than the degree of swelling when the crosslinked silicone resin is immersed in the second liquid.
  • the second liquid can be miscible with the first liquid.
  • One embodiment of the present invention is a wet gel manufacturing method, wherein a silicone resin composition can be dissolved in a first liquid capable of dissolving the silicone resin composition, and the first liquid.
  • a solid or a second liquid having a degree of swelling when the crosslinked silicone resin in which the silicone resin composition is cured is immersed is less than the degree of swelling when the crosslinked silicone resin is immersed in n-dodecane.
  • a wet gel that is not limited to a liquid having a predetermined affinity for a polymer, has excellent adhesion, and can be separated spontaneously. Can do.
  • 4 is a photograph showing evaluation results of difficulty adhesion of the wet gel of Example 1-1 and the crosslinked silicone resin of Comparative Example 1 to mayonnaise.
  • 4 is a photograph showing evaluation results of difficulty adhesion of the wet gel of Example 1-1 and the crosslinked silicone resin of Comparative Example 1 to mayonnaise.
  • 3 is a photograph showing evaluation results of difficulty adhesion of wet gel of Example 1-1 and crosslinked silicone resin of Comparative Example 1 to ketchup.
  • 3 is a photograph showing evaluation results of difficulty adhesion of wet gel of Example 1-1 and crosslinked silicone resin of Comparative Example 1 to ketchup.
  • the wet gel is a crosslinked silicone resin in which the silicone resin composition is cured, a first liquid capable of dissolving the silicone resin composition, a solid capable of dissolving in the first liquid, or And a second liquid having a degree of swelling when dipping the crosslinked silicone resin is less than the degree of swelling when dipping the crosslinked silicone resin in n-dodecane.
  • the second liquid can be mixed with the first liquid.
  • the liquid capable of dissolving the silicone resin composition means a liquid that becomes a transparent solution without phase separation when mixed with the silicone resin composition. means.
  • the solid that can be dissolved in the first liquid means a liquid that becomes a transparent solution when mixed with the first liquid.
  • the second liquid is miscible with the first liquid.
  • the second liquid becomes a transparent mixed solution without phase separation. Means.
  • the wet gel prevents liquids such as water and oil from coming into direct contact with the wet gel and has excellent adhesion. Moreover, even if the liquid separated on the surface of the wet gel is removed with cotton, alcohol or the like, or oxidatively decomposed with oxygen plasma or the like, the wet gel gradually separates. For this reason, the surface of the wet gel is again coated with the detached liquid.
  • the cross-linked silicone resin is an elastic body, the volume of the wet gel decreases with the separation. When the separated liquid reacts with moisture in the atmosphere and solidifies, the surface of the wet gel is covered with the generated solid.
  • the wet gel gradually separates, so that the surface of the wet gel is covered again with the produced solid. Further, when the separated liquid contains a solid, the surface of the wet gel is covered with the solid. At this time, the solid may self-assemble to form a fractal microstructure, and the surface of the wet gel may exhibit super water repellency. In this case as well, even if the solid generated on the surface of the wet gel is removed or the wet gel is cut, the wet gel is continuously and gradually separated, so that the surface of the wet gel is generated. It is again coated with a solid.
  • the detachment may be induced by a change with time of the crosslinked silicone resin contained in the wet gel or a change with time of the first liquid and / or the second liquid.
  • the first liquid does not serve as the second liquid, it is possible to promote separation by volatilizing the first liquid having a vapor pressure higher than that of the second liquid.
  • the wet gel when the wet gel is cooled, the wet gel may lose transparency. This is considered to be because light is scattered by promoting phase separation between the first liquid and the crosslinked silicone resin inside the wet gel.
  • the wet gel can be produced by curing the silicone resin composition in the presence of the first liquid and a solid that can be dissolved in the first liquid or the second liquid.
  • the silicone resin composition preferably contains a compound having a vinyl group and a compound having a hydrosilyl group. Accordingly, when the silicone resin composition is cured, the hydrosilylation reaction proceeds and a crosslinked silicone resin is generated.
  • silicone resin having a vinyl group examples include modified polydimethylsiloxane and polymethylvinylsiloxane in which vinyl groups are introduced at both ends.
  • Examples of the metal alkoxide having a vinyl group include vinyltriethoxysilane and allyltriethoxysilane.
  • the compound having a hydrosilyl group is not particularly limited, and examples thereof include a silicone resin having a hydrosilyl group and a metal alkoxide having a hydrosilyl group.
  • silicone resin having a hydrosilyl group examples include dimethylmethyl hydrogen polysiloxane.
  • Examples of the metal alkoxide having a hydrosilyl group include triethoxysilane and trimethoxysilane.
  • a platinum-based catalyst When curing the silicone resin composition, a platinum-based catalyst may be used.
  • the silicone resin composition When the silicone resin composition is cured, the silicone resin composition, the first liquid, the solid that can be dissolved in the first liquid, or the liquid containing the second liquid is usually transparent. is there.
  • the silicone resin composition When the silicone resin composition is cured, it may be heated.
  • the temperature at which the silicone resin composition is cured can be appropriately controlled according to the amount of the catalyst added, but is usually 20 to 150 ° C.
  • the first liquid is not particularly limited, and examples include alkane, silicone oil, polymethylphenylsiloxane, toluene, tetraalkoxysilane, and polyalkoxysiloxane.
  • the alkoxy group is hydrolyzed in the presence of an acid or a base, and the affinity with the crosslinked silicone resin is lowered. It is possible to behave.
  • alkanes examples include n-decane, n-dodecane, n-tetradecane, n-hexadecane, and isocetane.
  • the solid that can be dissolved in the first liquid is not particularly limited, and examples thereof include tristearin and a lotus leaf extract.
  • Examples of the second liquid include, but are not limited to, n-tetradecane, n-hexadecane, trichlorooctadecylsilane, polymethylphenylsiloxane, phenylmethylsiloxane-dimethylsiloxane copolymer, and the like.
  • the second liquid may also serve as the first liquid.
  • the wet gel is usually transparent and has plasticity.
  • the first liquid does not serve as the second liquid
  • the first liquid volatilizes, the affinity between the first liquid and the second liquid and the crosslinked silicone resin is reduced, and separation is promoted.
  • the wet gel may further contain particles. Thereby, the hardness and bactericidal property of the wet gel can be improved, and the light transmission property can be adjusted.
  • the particles are not particularly limited, and examples thereof include silica particles, alumina particles, zirconia particles, silver particles, gold particles, platinum particles, and magnetic particles.
  • the particle may have a vinyl group, a hydrosilyl group or the like introduced on the surface. Thereby, particle
  • the wet gel can be produced by curing the silicone resin composition in the presence of the first liquid and the solid or the second liquid.
  • wet gel may be used as it is, or may be used by forming on a solid surface.
  • the solid may have a vinyl group, hydrosilyl group or the like introduced on the surface. Thereby, the adhesion between the wet gel and the solid can be strengthened.
  • a part means a mass part.
  • V 0 the volume of the crosslinked silicone resin, the volume of the crosslinked silicone resin after immersion in a liquid and V, Formula V / V 0 From this, the degree of swelling was calculated.
  • Table 1 shows the degree of swelling of the liquid.
  • Example 1-1 1 part of Sylgard 184 (manufactured by Dow Corning) and 0.1 part of Sylgard 184 curing agent (manufactured by Dow Corning) as a silicone resin composition, 3 parts of n-hexadecane as the first liquid also serving as the second liquid Were mixed to obtain a transparent precursor solution. Next, using an oven, the precursor solution was heated at 100 ° C. for 2 hours to cure the silicone resin composition to obtain a wet gel. The wet gel was transparent and had plasticity.
  • Sylgard 184 main agent is a modified polydimethylsiloxane having vinyl groups introduced at both ends, a surface-treated silica filler having 2,2-dimethylvinyl group, 1,2-dimethylvinyl group and trimethylmethyl group introduced on the surface, Includes tetrakis (trimethylsiloxy) silane, ethylbenzene, and platinum-based catalyst.
  • Sylgard 184 curing agent is dimethylmethyl hydrogen polysiloxane, modified polydimethylsiloxane having vinyl groups introduced at both ends, 2,4,6,8-tetramethyl-2,4,6,8-tetravinylcyclotetra It contains ethylbenzene, a surface-treated silica filler in which siloxane, 2,2-dimethylvinyl group, 1,2-dimethylvinyl group and trimethylmethyl group are introduced on the surface.
  • n-hexadecane was able to dissolve the silicone resin composition.
  • Examples 1-2 to 1-9 Except for changing the addition amount of n-hexadecane to 1.5 parts, 2 parts, 2.5 parts, 5 parts, 7 parts, 9 parts, 12 parts, 19 parts, the same as in Example 1-1, A wet gel was obtained. The wet gel was transparent and had plasticity.
  • Examples 1-10 to 1-12 instead of n-hexadecane, polymethylphenylsiloxane CR100 (manufactured by Sigma-Aldrich), polymethylphenylsiloxane TSF431 (manufactured by MOMENTIVE), phenylmethylsiloxane-dimethylsiloxane copolymer AS100 (manufactured by Sigma-Aldrich) is used.
  • a wet gel was obtained in the same manner as Example 1-1 except that. The wet gel was transparent and had plasticity.
  • CR100, TSF431, and AS100 were able to dissolve the silicone resin composition.
  • the wet gels of Examples 1-10 to 1-12 were separated when left for 1 hour.
  • the wet gels of Examples 1-10 to 1-12 were cut and allowed to stand for 1 hour, the wet gel was separated from the cut surface, and the separation continued for 3 months or more.
  • the wet gels of Examples 1-10 to 1-12 were roughened with a cutter knife and the transparency was lowered, the transparency of the surface was recovered by separation.
  • Example 1 was repeated except that n-hexane, n-octane, n-decane, n-dodecane, toluene and tetraethoxysilane were used as the first liquid instead of n-hexadecane. A wet gel was obtained. The wet gel was transparent and had plasticity.
  • n-hexane, n-octane, n-decane, n-dodecane, toluene, and tetraethoxysilane were able to dissolve the silicone resin composition.
  • FIG. 1 shows the evaluation results of difficulty adhesion to the mayonnaise of the wet gel of Example 1-1 and the crosslinked silicone resin of Comparative Example 1.
  • 1A and 1B show a wet gel and a crosslinked silicone resin before and after the mayonnaise is attached to the surface and then inclined.
  • FIG. 2 shows the evaluation results of difficulty adhesion to the ketchup of the wet gel of Example 1-1 and the crosslinked silicone resin of Comparative Example 1.
  • 2A and 2B show the wet gel and the crosslinked silicone resin before and after the ketchup is attached to the surface and then inclined.
  • Example 1-1 does not adhere mayonnaise and ketchup to the surface and has excellent adhesion to mayonnaise and ketchup.
  • the wet gels of Examples 1-2 to 1-12 were excellent in difficult adhesion to mayonnaise and ketchup, similar to the wet gel of Example 1-1.
  • the wet gels of Comparative Examples 2 to 7 had poor adhesion properties to mayonnaise and ketchup, similar to the crosslinked silicone resin of Comparative Example 1.
  • the wet gels of Examples 1-1 to 1-12 temporarily decreased the difficulty of sticking to mayonnaise when the release layer was wiped off, but after the passage of time, the same as before the release layer was wiped off. It showed poor adhesion to mayonnaise.
  • wet gels of Examples 1-1 to 1-12 were able to easily remove the dried fixed matter even when the mayonnaise and ketchup adhering to the surface were dried by heating.
  • Example 2-1 Example 1-1, except that 0.38 part of n-decane as the first liquid and 1.13 part of n-hexadecane as the second liquid were used instead of 3 parts of n-hexadecane Similarly, a wet gel was obtained. The wet gel was transparent and had plasticity.
  • n-decane was able to dissolve the silicone resin composition. Also, n-hexadecane could be mixed with n-decane.
  • Example 2-2 A wet gel was obtained in the same manner as in Example 2-1, except that the addition amounts of n-decane and n-hexadecane were changed to 0.15 parts and 1.35 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 2-3 A wet gel was obtained in the same manner as in Example 2-1, except that the addition amounts of n-decane and n-hexadecane were changed to 0.08 parts and 1.42 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 2-4 A wet gel was obtained in the same manner as in Example 2-1, except that the addition amounts of n-decane and n-hexadecane were changed to 0.75 parts and 2.25 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 2-5 A wet gel was obtained in the same manner as in Example 2-1, except that the addition amounts of n-decane and n-hexadecane were changed to 0.3 parts and 2.7 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 2-6 A wet gel was obtained in the same manner as in Example 2-1, except that the addition amounts of n-decane and n-hexadecane were changed to 0.16 parts and 2.84 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • the wet gels of Examples 2-1 to 2-6 were excellent in difficult adhesion to mayonnaise and ketchup in the same manner as the wet gel of Example 1-1.
  • Example 3-1 Example 1-1, except that 0.08 part of n-dodecane as the first liquid and 1.42 part of n-hexadecane as the second liquid were used instead of 3 parts of n-hexadecane. Similarly, a wet gel was obtained. The wet gel was transparent and had plasticity.
  • n-dodecane was able to dissolve the silicone resin composition. Also, n-hexadecane could be mixed with n-dodecane.
  • Example 3-2 A wet gel was obtained in the same manner as in Example 3-1, except that the addition amounts of n-dodecane and n-hexadecane were changed to 0.6 parts and 5.4 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 3-3 A wet gel was obtained in the same manner as in Example 3-1, except that the addition amounts of n-dodecane and n-hexadecane were changed to 0.32 parts and 5.68 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 3-4 A wet gel was obtained in the same manner as in Example 3-1, except that the addition amounts of n-dodecane and n-hexadecane were changed to 0.16 parts and 2.84 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • the wet gels of Examples 3-1 to 3-4 were excellent in difficult adhesion to mayonnaise and ketchup.
  • Example 4-1 Similar to Example 1-1, except that 0.08 part of n-tetradecane and 1.42 part of n-hexadecane were used instead of 3 parts of n-hexadecane as the first liquid also serving as the second liquid. Thus, a wet gel was obtained. The wet gel was transparent and had plasticity.
  • n-tetradecane and n-hexadecane were able to dissolve the silicone resin composition. Further, n-hexadecane could be mixed with n-tetradecane.
  • Example 4-2 A wet gel was obtained in the same manner as in Example 4-1, except that the addition amounts of n-tetradecane and n-hexadecane were changed to 0.63 parts and 11.37 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 4-3 A wet gel was obtained in the same manner as in Example 4-1, except that the addition amounts of n-tetradecane and n-hexadecane were changed to 0.32 parts and 5.68 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 4-4 A wet gel was obtained in the same manner as in Example 4-1, except that the addition amounts of n-tetradecane and n-hexadecane were changed to 0.16 parts and 2.84 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 5-1 Instead of 3 parts of n-hexadecane, polymethylphenylsiloxane PMM-0021 (manufactured by Gelest Co.) 0 as a first liquid that also serves as the second liquid, 0.8 part of n-decane as the first liquid A wet gel was obtained in the same manner as Example 1-1 except that 2 parts were used. The wet gel was transparent and had plasticity.
  • n-decane and PMM-0021 were able to dissolve the silicone resin composition.
  • PMM-0021 could be mixed with n-decane.
  • Example 5-2 A wet gel was obtained in the same manner as in Example 5-1, except that the addition amounts of n-decane and PMM-0021 were changed to 1.8 parts and 1.2 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 5-3 A wet gel was obtained in the same manner as in Example 5-1, except that the addition amounts of n-decane and PMM-0021 were changed to 1.2 parts and 1.8 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 5-4 A wet gel was obtained in the same manner as in Example 5-1, except that the addition amounts of n-decane and PMM-0021 were changed to 0.6 parts and 2.4 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 5-5 A wet gel was obtained in the same manner as in Example 5-1, except that the addition amounts of n-decane and PMM-0021 were changed to 2.4 parts and 1.6 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 5-6 A wet gel was obtained in the same manner as in Example 5-1, except that the addition amounts of n-decane and PMM-0021 were changed to 0 part and 3.0 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • the wet gels of Examples 5-1 to 5-6 were excellent in difficult adhesion to mayonnaise and ketchup.
  • Example 6 Instead of 3 parts of n-hexadecane, 3 parts of n-dodecane as the first liquid and 1 part of polymethylphenylsiloxane PMM-0021 (manufactured by Gelest) as the first liquid also serving as the second liquid A wet gel was obtained in the same manner as Example 1-1 except that it was used. The wet gel was transparent and had plasticity.
  • n-dodecane and PMM-0021 were able to dissolve the silicone resin composition.
  • PMM-0021 could be mixed with n-dodecane.
  • Example 6 When the wet gel of Example 6 was allowed to stand for 1 hour, the wet gel was separated. At this time, when the wet gel was cooled, the release was promoted, while when the wet gel was heated, the release was suppressed. When the wet gel of Example 6 was cut and left for 1 hour, the wet gel was separated from the cut surface.
  • the wet gel of Example 6 was excellent in difficult adhesion to mayonnaise and ketchup.
  • Example 7-1 Example 1 except that 3 parts of n-tetradecane and 1 part of polymethylphenylsiloxane PMM-0021 (manufactured by Gelest) were used instead of 3 parts of n-hexadecane as the first liquid that also served as the second liquid. A wet gel was obtained in the same manner as in 1-1. The wet gel was transparent and had plasticity.
  • n-tetradecane and PMM-0021 were able to dissolve the silicone resin composition.
  • PMM-0021 could be mixed with n-tetradecane.
  • Example 7-2 A wet gel was obtained in the same manner as in Example 7-1 except that the addition amounts of n-tetradecane and PMM-0021 were changed to 0.75 parts and 0.25 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 7-3 A wet gel was obtained in the same manner as in Example 7-1 except that the addition amounts of n-tetradecane and PMM-0021 were changed to 1.5 parts and 0.5 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 7-4 A wet gel was obtained in the same manner as in Example 7-1 except that the addition amounts of n-tetradecane and PMM-0021 were changed to 2.25 parts and 0.75 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 7-1 to 7-4 were excellent in difficult adhesion to mayonnaise and ketchup in the same manner as the wet gel of Example 1-1.
  • Example 8 Example except that 3 parts of n-hexadecane and 1 part of polymethylphenylsiloxane PMM-0021 (manufactured by Gelest) were used instead of 3 parts of n-hexadecane as the first liquid also serving as the second liquid. A wet gel was obtained in the same manner as in 1-1. The wet gel was transparent and had plasticity.
  • n-hexadecane and PMM-0021 can dissolve the silicone resin composition and cannot swell the crosslinked silicone resin.
  • PMM-0021 could be mixed with n-tetradecane.
  • Example 8 When the wet gel of Example 8 was allowed to stand for 1 hour, the wet gel was separated. At this time, when the wet gel was cooled, the release was promoted, while when the wet gel was heated, the release was suppressed. When the wet gel of Example 8 was cut and left for 1 hour, the wet gel was separated from the cut surface.
  • the wet gel of Example 8 was excellent in difficult adhesion to mayonnaise and ketchup.
  • Example 9 Instead of 3 parts of n-hexadecane, 2.8 parts of isocetane as the first liquid, polymethylphenylsiloxane PMM-0021 (manufactured by Gelest) 1.2 as the first liquid also serving as the second liquid A wet gel was obtained in the same manner as Example 1-1 except that the parts were used. The wet gel was transparent and had plasticity.
  • isocetane and PMM-0021 were able to dissolve the silicone resin composition. Moreover, PMM-0021 could be mixed with isocetane.
  • Example 9 When the wet gel of Example 9 was allowed to stand for 1 hour, the wet gel was separated. At this time, when the wet gel was cooled, the release was promoted, while when the wet gel was heated, the release was suppressed. When the wet gel of Example 9 was cut and left for 1 hour, the wet gel was separated from the cut surface.
  • the wet gel of Example 9 was excellent in difficult adhesion to mayonnaise and ketchup. Further, the wet gel of Example 9 was excellent in difficult adhesion to ice, similar to the wet gel of Example 5-1.
  • Example 10-1 Instead of 3 parts of n-hexadecane, 0.6 part of polymethylphenylsiloxane AR20 (manufactured by Sigma-Aldrich) as the first liquid also serving as the second liquid, polymethylphenylsiloxane as the second liquid A wet gel was obtained in the same manner as in Example 1-1 except that 2.4 parts of TSF437 (manufactured by MOMENTIVE) was used. The wet gel was transparent and had plasticity.
  • polymethylphenylsiloxane AR20 manufactured by Sigma-Aldrich
  • TSF437 manufactured by MOMENTIVE
  • AR20 was able to dissolve the silicone resin composition.
  • TSF437 could be mixed with AR20.
  • Example 10-2 A wet gel was obtained in the same manner as in Example 10-1, except that the addition amounts of AR20 and TSF437 were changed to 0.9 parts and 2.1 parts, respectively. The wet gel was transparent and had plasticity.
  • Example 10-3 A wet gel was obtained in the same manner as in Example 10-1, except that the addition amounts of AR20 and TSF437 were changed to 1.2 parts and 1.8 parts, respectively. The wet gel was transparent and had plasticity.
  • Example 10-4 A wet gel was obtained in the same manner as in Example 10-1, except that the addition amounts of AR20 and TSF437 were changed to 1.8 parts and 1.2 parts, respectively. The wet gel was transparent and had plasticity.
  • the wet gels of Examples 10-1 to 10-4 were excellent in difficult adhesion to mayonnaise and ketchup.
  • Example 10-5 A wet gel was obtained in the same manner as in Example 10-1, except that the addition amounts of AR20 and TSF437 were changed to 2.1 parts and 0.9 parts, respectively. The wet gel was transparent and had plasticity.
  • Example 10-6 A wet gel was obtained in the same manner as in Example 10-1, except that the addition amounts of AR20 and TSF437 were changed to 2.25 parts and 0.75 parts, respectively. The wet gel was transparent and had plasticity.
  • Example 10-7 A wet gel was obtained in the same manner as in Example 10-1, except that the addition amounts of AR20 and TSF437 were changed to 2.4 parts and 0.6 parts, respectively. The wet gel was transparent and had plasticity.
  • Example 10-8 A wet gel was obtained in the same manner as in Example 10-1, except that the addition amounts of AR20 and TSF437 were changed to 3 parts and 0 parts, respectively, and AR20 was used as the first liquid that also served as the second liquid. It was. The wet gel was transparent and had plasticity.
  • Example 10-8 had an adhesion to ice of 3 kPa.
  • Example 10-6 The wet gel of Example 10-6 was separated at below freezing. In addition, the wet gel of Example 10-6 had an adhesion force to ice of 0.4 kPa. Further, when the surface of the wet gel of Example 10-6 was tilted by 20 °, the ice slipped off due to its own weight. Thus, it was found that the wet gel of Example 10-6 was excellent in difficult adhesion.
  • the crosslinked silicone resin of Comparative Example 1 had an adhesion force to ice of 74.1 kPa.
  • the wet gel of Comparative Example 6 had an adhesion force to ice of 16.7 kPa.
  • the wet gels of Examples 10-3 to 10-5 had an adhesion rate of seaweeds of 10% or less, and were excellent in difficult adhesion to seaweeds.
  • the cross-linked silicone resin of Comparative Example 1 had an adhesion rate of seaweeds of 50% or more, and was inferior in adhesion to seaweeds.
  • Example 11-1 A wet gel was obtained in the same manner as in Example 1-1 except that 4 parts of toluene as a first liquid and 0.04 part of tristearin as a solid were used instead of 3 parts of n-hexadecane. It was. The wet gel was transparent and had plasticity.
  • Example 11-2 A wet gel was obtained in the same manner as in Example 11-1, except that the amount of tristearin added was changed to 0.03 part. The wet gel was transparent and had plasticity.
  • Example 11-3 A wet gel was obtained in the same manner as in Example 11-1, except that the addition amounts of toluene and tristearin were changed to 3 parts and 0.01 parts, respectively. The wet gel was transparent and had plasticity.
  • Example 11-4 A wet gel was obtained in the same manner as in Example 11-1, except that the addition amounts of toluene and tristearin were changed to 3 parts and 0.03 parts, respectively. The wet gel was transparent and had plasticity.
  • Example 11-5 A wet gel was obtained in the same manner as in Example 11-1, except that the addition amounts of toluene and tristearin were changed to 3 parts and 0.06 parts, respectively. The wet gel was transparent and had plasticity.
  • Example 11-6 A wet gel was obtained in the same manner as in Example 11-1, except that the addition amounts of toluene and tristearin were changed to 3 parts and 0.12 parts, respectively. The wet gel was transparent and had plasticity.
  • Example 11-7 A wet gel was obtained in the same manner as in Example 11-1, except that the addition amounts of toluene and tristearin were changed to 3 parts and 0.24 parts, respectively. The wet gel was transparent and had plasticity.
  • Example 11-8 A wet gel was obtained in the same manner as in Example 11-1, except that 3 parts of a solution obtained by saturating lotus leaf extract in toluene was used instead of 4 parts of toluene and 0.04 part of tristearin. .
  • the wet gel was transparent and had plasticity.
  • the wet gels of Examples 11-1 to 11-8 were excellent in difficult adhesion to mayonnaise and ketchup.
  • the wet gel of Example 11-1 was transparent and had a static contact angle with respect to water of about 100 °. However, the surface became cloudy with separation, and the static contact angle with respect to water was 150 ° or more. And showed super water repellency. For this reason, it was found that the wet gel of Example 11-1 was excellent in difficult adhesion to water. Further, when the wet gel of Example 11-1 was cut, the cut surface became cloudy as it separated and showed super water repellency.
  • the wet gels of Examples 11-2 to 11-8 were excellent in difficult adhesion to water.
  • Example 12 Example 1-1 was used except that 2.4 parts of n-decane as the first liquid and 0.6 part of trichlorooctadecylsilane as the second liquid were used instead of 3 parts of n-hexadecane. Similarly, a wet gel was obtained. The wet gel was transparent and had plasticity.
  • n-decane was able to dissolve the silicone resin composition. Further, trichlorooctadecylsilane could be mixed with n-decane.
  • the wet gel of Example 12 was excellent in difficult adhesion to mayonnaise and ketchup.
  • the wet gel of Example 12 was excellent in difficult adhesion to water, similar to the wet gel of Example 11-1.
  • Example 13 Example 1-1 and Example 1-1 were used except that 2.9 parts of n-dodecane as the first liquid and 0.1 part of trichlorooctadecylsilane as the second liquid were used instead of 3 parts of n-hexadecane. Similarly, a wet gel was obtained. The wet gel was transparent and had plasticity.
  • n-dodecane was able to dissolve the silicone resin composition. Further, trichlorooctadecylsilane could be mixed with n-dodecane.
  • the wet gel of Example 13 had excellent adhesion to mayonnaise and ketchup, similar to the wet gel of Example 1-1. In addition, the wet gel of Example 13 was excellent in difficult adhesion to water, similar to the wet gel of Example 11-1.
  • Example 14 Example 3 except that 4 parts of n-tetradecane as the first liquid also serving as the second liquid and 0.06 part of trichlorooctadecylsilane as the second liquid were used instead of 3 parts of n-hexadecane A wet gel was obtained in the same manner as in 1-1. The wet gel was transparent and had plasticity.
  • n-tetradecane was able to dissolve the silicone resin composition. Further, trichlorooctadecylsilane could be mixed with n-tetradecane.
  • the wet gel of Example 14 was excellent in difficult adhesion to mayonnaise and ketchup. In addition, the wet gel of Example 14 was excellent in poor adhesion to water, similar to the wet gel of Example 11-1.
  • Example 15 Example 1 was repeated except that 2.25 parts of isocetane as the first liquid and 0.75 parts of trichlorooctadecylsilane as the second liquid were used instead of 3 parts of n-hexadecane. Thus, a wet gel was obtained. The wet gel was transparent and had plasticity.
  • isocetane was able to dissolve the silicone resin composition.
  • trichlorooctadecylsilane could be mixed with isocetane.
  • the wet gel of Example 15 was excellent in difficult adhesion to mayonnaise and ketchup, similar to the wet gel of Example 1-1. In addition, the wet gel of Example 15 was excellent in poor adhesion to water, similar to the wet gel of Example 11-1.
  • Example 16-1 Similar to Example 1-1, except that 0.15 part of a 1% by mass n-hexane dispersion of gold particles having an average particle size of 10 nm (manufactured by Shikoku Keiki Kogyo Co., Ltd.) was further added when preparing the precursor solution. Thus, a wet gel was obtained. The wet gel was transparent and had plasticity.
  • n-hexane was the first solvent and was able to dissolve the silicone resin composition.
  • Example 16-2 Except for using a 1% by mass hexane dispersion of platinum particles having an average particle size of 10 nm (manufactured by Shikoku Keiki Kogyo Co., Ltd.) instead of the 1% by mass n-hexane dispersion of gold particles having an average particle size of 10 nm A wet gel was obtained in the same manner as in Example 16-1. The wet gel was transparent and had plasticity.
  • Example 16-1 and 16-2 were excellent in difficult adhesion to mayonnaise and ketchup in the same manner as the wet gel of Example 1-1.
  • Example 8-1 A wet gel in the same manner as in Example 1-1 except that 2.4 parts of tetraethoxysilane and 0.6 parts of octyltriethoxysilane were used as the first liquid instead of 3 parts of n-hexadecane. Got. The wet gel was transparent and had plasticity.
  • Comparative Example 8-2 A wet gel was obtained in the same manner as in Comparative Example 8-1, except that the addition amounts of tetraethoxysilane and octyltriethoxysilane were changed to 2.1 parts and 0.9 parts, respectively. The wet gel was transparent and had plasticity.
  • Comparative Example 8-3 A wet gel was obtained in the same manner as in Comparative Example 8-1, except that the addition amounts of tetraethoxysilane and octyltriethoxysilane were changed to 1.8 parts and 1.2 parts, respectively. The wet gel was transparent and had plasticity.
  • Comparative Example 8-4 A wet gel was obtained in the same manner as in Comparative Example 8-1, except that the addition amounts of tetraethoxysilane and octyltriethoxysilane were changed to 1.5 parts and 1.5 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Comparative Example 8-5 A wet gel was obtained in the same manner as in Comparative Example 8-1, except that the addition amounts of tetraethoxysilane and octyltriethoxysilane were changed to 1.2 parts and 1.8 parts, respectively. The wet gel was transparent and had plasticity.
  • Comparative Example 8-6 A wet gel was obtained in the same manner as in Comparative Example 8-1, except that the addition amounts of tetraethoxysilane and octyltriethoxysilane were changed to 0.9 parts and 2.1 parts, respectively. The wet gel was transparent and had plasticity.
  • Comparative Example 8-7 A wet gel was obtained in the same manner as in Comparative Example 8-1, except that the addition amounts of tetraethoxysilane and octyltriethoxysilane were changed to 0.6 parts and 2.4 parts, respectively. The wet gel was transparent and had plasticity.
  • Comparative Example 8-8 A wet gel was obtained in the same manner as in Comparative Example 8-1, except that the addition amounts of tetraethoxysilane and octyltriethoxysilane were changed to 0.3 parts and 2.7 parts, respectively. The wet gel was transparent and had plasticity.
  • Example 17-1 Instead of using 3 parts of n-hexadecane, 0.3 part of n-decane as the first liquid and 2.7 parts of polyphenylmethylsiloxane TSF437 (manufactured by MOMENTIVE) as the second liquid were used. A wet gel was obtained in the same manner as in Example 1-1. The wet gel was transparent and had plasticity.
  • n-decane was able to dissolve the silicone resin composition.
  • polyphenylmethylsiloxane could be mixed with n-decane.
  • Example 17-2 A wet gel was obtained in the same manner as in Example 17-1, except that the addition amounts of n-decane and TSF437 were changed to 0.6 parts and 2.4 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 17-3 A wet gel was obtained in the same manner as in Example 17-1, except that the addition amounts of n-decane and TSF437 were changed to 0.9 parts and 2.1 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 17-4 A wet gel was obtained in the same manner as in Example 17-1, except that the addition amounts of n-decane and TSF437 were changed to 1.2 parts and 1.8 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 17-5 A wet gel was obtained in the same manner as in Example 17-1, except that the addition amounts of n-decane and TSF437 were changed to 1.5 parts and 1.5 parts, respectively.
  • the wet gel was transparent and had plasticity.
  • Example 17-6 A wet gel was obtained in the same manner as in Example 17-1, except that the addition amounts of n-decane and TSF437 were changed to 1.8 parts and 1.2 parts, respectively. The wet gel was transparent and had plasticity.
  • Example 17-7 A wet gel was obtained in the same manner as in Example 17-1, except that the addition amounts of n-decane and TSF437 were changed to 2.1 parts and 0.9 parts, respectively. The wet gel was transparent and had plasticity.
  • the wet gels of Examples 17-1 to 17-7 were excellent in difficult adhesion to mayonnaise and ketchup.
  • Example 18-1 Polymethylphenylsiloxane AR20 as a first liquid that also serves as the second liquid, 1 part of Sylgard 184 (manufactured by Dow Corning) and 0.1 part of Sylgard 184 curing agent (manufactured by Dow Corning) as a silicone resin composition 3 parts (manufactured by Sigma-Aldrich) were mixed to obtain a transparent precursor solution. Next, 4 ⁇ 10 ⁇ 4 parts of Karsted catalyst was added, and then allowed to stand at room temperature for 5 minutes to cure the silicone resin composition to obtain a wet gel. The wet gel was transparent and had plasticity.
  • Example 18-2 A wet gel was obtained in the same manner as in Example 18-1, except that the amount of added Karsted catalyst was changed to 4 ⁇ 10 ⁇ 5 parts and allowed to stand at room temperature for 4 hours. The wet gel was transparent and had plasticity.
  • the wet gels of Examples 18-1 and 18-2 were excellent in difficult adhesion to mayonnaise and ketchup.

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Abstract

La présente invention décrit sous un aspect un gel humide comprenant : une résine de silicone réticulé obtenue par durcissement d'une composition de résine de silicone; un premier liquide capable de dissoudre la composition de résine de silicone; et un second liquide, miscible avec le premier liquide, où le degré de gonflement lorsque la résine de silicone réticulé ou un objet solide pouvant être dissous dans le premier liquide est immergé(e) dans le second liquide est inférieur au degré de gonflement lorsque la résine de silicone réticulé est immergée dans du n-dodécane.
PCT/JP2015/067728 2014-06-24 2015-06-19 Gel humide et son procédé de fabrication WO2015198985A1 (fr)

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US15/319,924 US10023701B2 (en) 2014-06-24 2015-06-19 Wet gel and method of producing thereof
EP15811115.3A EP3162857B1 (fr) 2014-06-24 2015-06-19 Gel humide et son procédé de fabrication
JP2016529542A JP6245714B2 (ja) 2014-06-24 2015-06-19 湿潤ゲル及びその製造方法
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CN106574119B (zh) 2020-06-12
JP6245714B2 (ja) 2017-12-13
EP3162857B1 (fr) 2020-11-18
US10023701B2 (en) 2018-07-17
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KR20170012398A (ko) 2017-02-02
EP3162857A1 (fr) 2017-05-03

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